A Product Person’s Perspective on Enterprise Selling

An architectural diagram for enterprise selling. ↗️

Many of the technical founders I have the opportunity to work with are well-versed in the architecture and features of their products (and products in general), but when it comes to possessing a similar view of the sales process there’s a good chance they are staring at a blank whiteboard. That’s to be expected because the skills and experience to do enterprise sales, and to do it well, are earned in the trenches over many years. Selling, specifically enterprise selling, is not something that comes naturally to most product-minded people.

Just as with code, one can devise an architectural view of how enterprise selling works. And like code, it is best to approach the process of selling using an architecture, rather than just diving in and writing code. Unlike code, if you act in haste or otherwise squander an enterprise opportunity there’s not really a chance for a rewrite or undo so it is best to approach with caution. Of course I’ve made many of my own mistakes and have also had ample time to learn what it was I have done wrong or what invalid assumptions I held. This post is a framework to help make sense of all the motions and actions that go on in the scope of enterprise sales.

Most technology leaders are consistently amazed at the depth and sophistication in enterprise selling. Since most engineers or technologists have little experience big-ticket selling, other than perhaps buying a car, this isn’t a surprise. While you might not be a designer or engineer, as a product person you have an empathy or sense of the skills, roles, and processes used. The same usually can’t be said for sales and selling.

There’s really only one key factor that distinguishes enterprise selling from everything a product person knows, and that is enterprise selling ends with the product and starts with the enterprise. Of course that is the complete opposite of what one might normally think where everything starts with a product. Even with the most amazing and inventive product ever conceived, selling at the enterprise level and enterprise scale requires inverting your perspective. There’s an analogy many often understand. Most product people know you don’t build a product by starting with a specific technology just because it is new, cool, or novel. Rather one starts by solving a problem of some sorts where applying a technology creates an amazing new experience that addresses a need or solves an articulated problem. Enterprise sales is similar in that you don’t start with a solution (your product) and then get to the problem (customer need, articulated or not).

Enterprise selling ends with the product and starts with the enterprise.

There are tons of amazing resources on enterprise selling. Resources go from the specifics of sales motions for a single sales person all the way to models for setting quotas, organizing resources, and training the sales organization. Most every seasoned enterprise sales person has their favorite toolset and part of hiring and managing a team is empowering them to make use of the tools they are comfortable with (just like you would for engineers). One resource I value is the book SPIN Selling, which is sort of a classic and spawned a whole ecosystem of supporting tools and guides.

A framework for product people

At an abstract level you can think of enterprise selling as following three steps:

First you set out to build a relationship with the enterprise customer that rests on a foundation of a deep understanding of their unique context. This relationship is formed by learning about the customer and organization, including how they do what they do, what they are struggling with and where they are heading. The biggest risk in most enterprise sales cycles is assuming you know these things—that one bank is like any other bank, that all Oracle shops are similar, or that everyone is trying to rip out SAP or move to the cloud. Almost all failures in enterprise selling, or at least all deal closing crisis moments, are caused by rushing this step or failing to learn all that needs to be learned about an enterprise.

Second, you articulate your vision or view of the “world” and how given your understanding of the enterprise you can begin to talk about a view for how to add value to an organization. The notion of “adding value” is key to this dialog as “solving problems” can set you up to fail too early in the process. The reason for this is that enterprise IT knows all to well that any new system begins with sunk costs, reduced productivity, and in general a period of investment. All this happens before the return or value is brought to the enterprise.

Finally, the last step is to establish a partnership, based on a mutual understanding. You understand the enterprise. The enterprise understands how you aim to aid value to their organization. The partnership process itself is how you go about going from pilot to implementation to expansion, sometimes called land and expand.

Let’s dive into each of these briefly with the goal of offering a flow or outline of the sorts of actions and motions that should take place. It is worth emphasizing that there’s a lot of unique value in how a given enterprise account manager approaches a specific customer with a specific type of product — so I’m not implying this is a one-size-fits-all model.

Relationship

The goal of the first milestone is a strong understanding of what things are like within the enterprise you are selling. To a product person this is very similar to those first ideas in developing a product-market fit and needing to assess the potential for the market. Much of the early effort will be consumed by understanding if you’re even working with the right team or people within an organization, and often there are multiple parties. Too often a product person believes you start at the CEO and shortcut this step, but an experienced account manager knows great deals can die in the middle of an organization just as easily at the top.

Culture. First you want to understand a bit of the culture of the enterprise. How risk averse they might be (for example, where do regulations fit or how leading edge is the organization as a whole)? You want to understand a bit about how decisions are made and how technologies and products are evaluated. You want to make sure you are sensitive to the basics of how the company likes to do business (how formal, what times do meetings take place, where do coffee, meals, drinks fit or don’t fit, and so on). This is especially true as you venture to industry segments that are unfamiliar to you. If you’ve ever done business in a different country before a good mindset to get in is to treat the initial contacts with an enterprise with the same level of cultural sensitivity and learning—better to learn rather than assume when you’re in an unfamiliar environment.

Organization. Every enterprise sales person I have worked with begins to build out the physical and logical org chart from the first engagements. You want to learn the management reporting structure as well as the power You want to understand the budget and decision making processes. Great enterprise sales people also know that you invest in the full org chart and don’t just focus on the areas of most authority and power—you never know where an advocate or obstacle might appear from as a deal progresses.

Infrastructure. IT is all about infrastructure and understanding how the company really works will be key to speaking their language. Not only are all enterprises subtly different in infrastructure, they take great pride in the differences they maintain and the rationale behind those differences, no matter how odd or crazy they might seem. I remember once pitching Office to an enterprise customer that had customized the installation of Office uniquely for over 100 different job functions. Not only did I think this was nuts, it created a massive support burden for the company. But in their world this was key to their productivity and my job was not to “save” them but to show them how I made their job even easier with a new product (all that comes later, in this step you’re just learning). You need to understand all the basics of infrastructure from authentication, networking, BYO, approved apps, messaging, email, and more many of these environmental variables will almost certainly impact your solution’s applicability and deployment.

Needs. Once you understand the culture, organization, and the technical infrastructure you have the foundation to be able to understand the enterprise’s needs. This is often the trickiest part of the first phase because it turns out enterprise IT, even though they are experts in technology, most often express their needs in terms of their own understanding or expectations of what products can do. As you catalog and understand needs what you are really doing is learning how to bridge from the solution your advocates believe they want to a solution that might be a much bigger leap (and much better, but very different) than expected. The pressure to listen to customers and act directly on needs (often described as requirements) is intense and during the course of product development and sales will be a significant challenge to just about every company.

My earliest days working with enterprise customers taught me a lesson that I have to admit still makes the “here and now” product person in me a bit uncomfortable. It was told to me by a former IBM field sales engineer who said “I sold more product today based on selling the future product than I ever sold by just selling what was ‘in my bag’.” While that’s most decidedly a cynical view, the reality is that enterprise selling is never about what a product can do right this moment—that’s just practical given the purchase, deployment, and training cycles within a large organization. Therefore a huge part of enterprise selling is articulating your unique technology/world view in the context of the relationship you have developed.

Vision

To many this can sound like selling vaporware, an old term for software that never shipped. That isn’t true at all. This is about selling a broad concept that will both endure for years and take years to fully realize, but can start delivering ROI in the near term within a known time period and cost. Putting this in the context of startups, this is much like when you hear venture capitalists talking about the investment in the team relative to the idea or invention—everyone knows the maze from idea to product to business will change and scope the initial idea, but the bet on the team and people will endure.

Inspiration. What is your inspiration for the product? This is where you talk about the experience that led you rethink the landscape. In the enterprise space this is most often about revisiting assumptions that the industry has made about costs of technology, where there is hardware versus software, or some massive shift such as the move to mobile or the cloud. Relative to a startup, you can think of this as the founder’s story—what led the founder to start a company is very much in line with what inspired the creation of a new enterprise product or service.

Uniqueness. While your inspiration is important it is likely that may people will have the same inspiration. In fact, enterprise products often appear in waves when it appears as though many are doing the “same” thing all at once. If you are in enterprise IT, then for sure every single vendor meeting you have these days is about cloud, mobile, BYO, security, and more. In a sales motion, you don’t want to spend a lot of time being the umteenth person touting the “changing world” but want to quickly articulate the insight, secret ingredient, or radical implementation that you have that you believe is unique. Too often this can be viewed as marketing, but really this needs to come from your product core—what is it that you see that no one else sees (to paraphrase Peter Thiel). Building a better mousetrap is great, but ROI in the enterprise does not come from rip and replace getting you a 10% improvement, so your inspiration should be pretty significant.

Competitors. You are not alone. No one in enterprise IT believes you built the one and only product that does most of what you do. Coming to an enterprise sales engagement with a detailed understanding of competitors shows respect and acknowledgement of reality. There are two types of competitors you need to understand fully. First, you need to be versed in the current marketplace competitors and how you compare to them. Often the best tool to view this is a classic “magic quadrant”—just be forewarned you have to substantiate claims carefully and be prepared for the “fans” of competitors to confront you (and be prepared for your competitors to sell against your characterization). If you’re doing this right, you are not creating new comparison criteria but using incumbent/competitor criteria as a starting point. Second, you need to be versed in how the enterprise is already addressing (or trying to address) the problem space. This is just as much a competitor—in enterprise software the easiest product to buy is the one you’ve already got in place and no one gets fired for doing that. While you might be negative towards your market competitors, it is incredibly important to be respectful of implemented competitors or homegrown solutions even if some in IT might mock their own choices.

Roadmap. The key deliverable for a vision is your roadmap of where you are heading. A roadmap to a product person might look like a schedule and features and some in IT most certainly would love that sort of information. In practice, the sort of tool you want to employ is much less detailed and granular than a product roadmap. Instead, you want to use a roadmap to establish a credible view for how you intend to both refine your existing proposition and expand your solution space. Why is this so critical? Enterprise IT is all about planning and long term within the organization. Budgets, headcount, organization, and internal service relationships all depend on “knowledge of the future”. At the same time, IT also wants to build new capabilities within the company and your roadmap can become a part of the IT roadmap. Obviously everything here is a fine balance between “promise and deliver” and falling into the trap of “over-promise and under-deliver”. One personal example was the introductions of both Outlook and Sharepoint and how adding them to the roadmap caused significant consternation in how IT thought of Office, which then crossed from personal productivity to messaging and then server infrastructure. In hindsight, the introduction of a product literally brought together parts of IT that previously never worked together!

Partnership

Transport yourself a couple of months (!) from that first opportunity to meet a potential customer and you’ve got a chance to really start to sell a product. For most product people, this is about deployment but to an enterprise account manager this last phase is about building a partnership. There is a distinction. The goal is to become long term partners and the tactic is to get the software into deployment and usage, not the other way around.

This phase always takes a bit longer than expected and for the first customers of a new product is a great deal of collaboration between engineering and sales. In later stages this repeatable process tends to become the role of Customer Success. For early stage products and companies, this phase is the equivalent of product-market fit as you work with the customer to refine the product (and pricing and more).

Proof. The first step is literally a proof of concept. The goal is to get the product up and running in their environment which could be as simple as single-sign on or a few dedicated clients or as complex as deployment or an isolated network with server hardware. It is likely during this stage that you will need to gain access to data, users, and systems that make the proof more relevant. It is important to be flexible and patient because for many pilots this is the most frustratingly slow part of the process. Do keep in mind, most every IT organization routinely does dozens of PoC, proof of concept, deals a year across many departments so be careful not to count this as “done” but do count it as “success”.

Implementation. The implementation phase is the time when you go from PoC to a deployed solution, aka production, within a department or company. For those building their first enterprise product, they are often shocked at how long it takes to roll out a new service or system within an enterprise even after it is running and working. We often compare this to signing up for a new SaaS service when in reality most companies are filled with employees that are far more worried about failing to get their work done than they are excited to try new tools and change the way they work. While many think most of the learning happens during the PoC, the astute enterprise product person knows that the real learning and informing of future product features takes place during the phased-in implementation when the product is in use by a wider audience outside of IT (if applicable).

Expansion. From a business perspective, the implementation counts as “land” and the next step is to “expand”. Once you’ve landed and seen early success, your advocates within IT will want to explore different ways to expand—remember IT is like everyone else and when something goes well they want to get credit and get visibility for the solution. Expansion is really the accelerator for a business and as most experienced people will tell you, there’s almost always more revenue with customers already paying you than with starting all over again with new potential customers. Enterprise products should be equipped in both the business and the product to expand in depth and breadth of usage to maximize this phase of growth. There’s potential for a bit of friction here as sales wants to keep the price down and not partition product value in order to land the deal. Management incentives across sales, marketing, product, and engineering play a critical role in finding this balance.

Replacement. The very last step in the partnership with an enterprise customer is replacing an existing system. I purposely put this last because most every product person thinks that when you have a new product the first line of sales is to explain what the customer can replace or decommission if they buy the new product. Every IT person knows that this is exactly the very last thing you do and that the long tail on usage for any implemented system before actual replacement, no matter how inevitable. This is important to internalize in terms of building a partnership because every running system has a champion or advocate who bought and deployed the system so a poor selling technique is to challenge that person too early. If you play everything correctly, someday you will be the system that keeps running long after it should—that’s something to keep in mind!

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If all of this seems like a lot of work and a great deal of calendar time, well then you read it correctly. Average enterprise sales cycles for seven figure sales are easily 3 months and often up to 9 months depending on pre-existing systems. While every once in a while there are shortcuts or magical products, by and large this is how enterprise selling goes. It also makes a lot of sense because you’re going to collect a lot of money every year and your product will become an important part of a business.